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3-叠氮香豆素与乙炔的荧光1,3-偶极环加成反应

A fluorogenic 1,3-dipolar cycloaddition reaction of 3-azidocoumarins and acetylenes.

作者信息

Sivakumar Krishnamoorthy, Xie Fang, Cash Brandon M, Long Su, Barnhill Hannah N, Wang Qian

机构信息

Department of Chemistry & Biochemistry, University of South Carolina, 631 Sumter Street, Columbia, SC 29208, USA.

出版信息

Org Lett. 2004 Nov 25;6(24):4603-6. doi: 10.1021/ol047955x.

Abstract

Copper(I)-catalyzed 1,3-dipolar cycloaddition reaction of nonfluorescent 3-azidocoumarins and terminal alkynes afforded intense fluorescent 1,2,3-triazole products. The mild condition of this reaction allowed us to construct a large library of pure fluorescent coumarin dyes. Since both azide and alkyne are quite inert to biological systems, this reaction has potential in bioconjugation and bioimaging applications. [reaction: see text]

摘要

铜(I)催化的非荧光3-叠氮香豆素与末端炔烃的1,3-偶极环加成反应生成了强荧光的1,2,3-三唑产物。该反应的温和条件使我们能够构建一个包含大量纯荧光香豆素染料的文库。由于叠氮化物和炔烃对生物系统都相当惰性,该反应在生物共轭和生物成像应用方面具有潜力。[反应:见正文]

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